Cesium carbonate → 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:19][OH:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][CH:37]=[CH:38][N:39]=2)=[CH:31][CH:30]=1.ClC1C=CC(S(N(CC2C=CC(C#N)=CC=2)[C@@H]2CCCCC[C@H]2CO)(=O)=O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:19][OH:20])[CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[O:36][CH:37]=[CH:38][N:39]=3)=[CH:33][CH:34]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Procedure
The title compound was synthesized from 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (80 mg, 0.25 mmol), cesium carbonate (164 mg, 0.50 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (72 mg, 0.30 mmol) according to the procedure described for 4-Chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (Example 40) to give 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (104 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.31 Hz), 7.73-7.75 (1H, m), 7.71-7.73 (1H, m), 7.69 (1H, s), 7.51 (1H, s), 7.48 (2H, s), 7.44-7.47 (1H, m), 7.21 (1H, s), 4.69 (1H, d, J=15.86 Hz), 3.99 (1H, d, J=15.61 Hz), 3.74-3.85 (1H, m), 3.67 (1H, dd, J=11.58, 4.28 Hz), 3.28 (1H, dd, J=11.58, 2.27 Hz), 2.27 (1H, br. s.), 1.42-1.65 (6H, m), 1.12-1.39 (5H, m). LC/MS R.T.=2.25 min; [M+H]+=475.22. HRMS [M+H]+ calc'd 475.1458, found 475.1459.
Sources & evidence
- ORD record
- ord-7d6942f81b6f42bc9e11eae69f1b9d7f
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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